


if i beg, you'll be the first to give

by honeyastral (hiraethseok)



Series: If I Bleed Series [2]
Category: Supernatural
Genre: Anal Sex, Butt Plugs, Dirty Talk, Dom Dean Winchester, Feminization, Gang Leader Dean Winchester, Hair-pulling, Incest Kink, M/M, Masturbation, Needy Sam Winchester, Orgasm Delay/Denial, Rimming, Sam Winchester Wears Panties, Sibling Incest, Sub Sam Winchester, Top Dean Winchester/Bottom Sam Winchester, Twink Sam Winchester, slight exhibitionism, whew chile these tags
Language: English
Status: Completed
Published: 2020-03-26
Updated: 2020-03-26
Packaged: 2021-03-01 03:14:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,161
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23238286
Author URL: https://archiveofourown.org/users/hiraethseok/pseuds/honeyastral
Summary: Sam was the one to ask about it, all big doe eyes and pouty lips and pink cheeks.“Wanna edge myself all day,” he’d whispered. “Get myself all desperate for you and then let you fuck me dry afterwards.” Dean had kissed him stupid and demanded he follow through.
Relationships: Dean Winchester/Sam Winchester
Series: If I Bleed Series [2]
Series URL: https://archiveofourown.org/series/1666555
Comments: 1
Kudos: 253





	if i beg, you'll be the first to give

**Author's Note:**

> sooo this is part two but u dont have to read part one to know whats going on!! 
> 
> this is just porn lol enjoy <3
> 
> comments/kudos make my day!!

.

“They took the entire west side of town,” Bobby mutters, casting a dark look at the setting sun through the window. Dean leans back in his seat and rubs his chin absently, staring down at the map spread and pinned across the table in front of them. “We can’t just sit still and twiddle our damn thumbs.”

Dean hums, glances up at Bobby with a furrow in his brow. 

“Obviously, we need to plan an attack, but I want to meet with the leader first. I doubt talking will do anything, but I’d rather tell him we’re gonna kick their asses and then prove it right. Sends a message to the other gangs in the area, doesn’t it?”

Bobby’s silent for a little while, and then he’s nodding. 

“S’pose that’s a nice start.”

“Great,” Dean says. “Now we need to figure out the specifics.” He looks up and around the room with a grin, clapping his hands together. “Any ideas?”

Before anyone can speak, however, Dean hears the soft pitter patter of footsteps scurrying down the hallway. He feels his lips pull slowly up into a sharp grin; he knows exactly who that is. 

Sammy rounds the corner just as he expects, cheeks rosy and eyes blown wide, and he looks like he’s just woken up, except Dean knows what’s really going on. He leans back in his seat, an easy smile on his face. 

“Sammy?” he calls. Sam chews his lower lip, and Dean can see the messy ruffle of his hair from rubbing up harsh against his pillow, tossing and turning and writhing. Dean licks his lips. 

“You wanna c’mere?” It’s an easy out; he can just shake his head _no_ and Dean will drop it, but Sam just pads over obediently to stand in front of Dean. 

Dean gives him a smile, eyes glinting, and then opens his arms. Sam’s eyes widen just a little, but he clambers onto Dean’s lap, tucks his head against Dean’s neck, breathes all shaky against his ear. 

“You good?” Dean whispers to him. Sam huffs, and Dean can _feel_ the heat of his glare. 

“Fuck off,” Sam mutters. Dean shuffles Sam on his lap, moves him so he’s straddling one of his thighs instead of balancing across both. Nobody else is close enough to hear Sam’s gasp, but Dean hears it just fine. 

His jeans are a little thick, but he can definitely feel it poking against his leg. Sam squirms, ears going hot, and Dean settles a hand on his back and steadies him, rubs soothing circles. 

“Calm down, angel,” he says lowly. “Don’t want anyone else knowing what a dirty little slut you are.” Sam tenses, body quivering, but Dean just smirks and turns to face the room again. 

“Sorry,” he says, tracing Sam’s spine. “He didn’t sleep that well last night. Where were we?”

Bobby quirks a brow, but he doesn’t ask. He’s learned not to. Dean just flashes a bright grin, and Bobby turns away. 

“Kevin?” he sighs. “You got any ideas?” Kevin blinks owlishly. 

“Yeah,” he says, hesitant. “I was just thinking, but I think I have some.” Bobby grins, crosses his arms in front of him. 

“Well then, let's hear them.”

Sam groans quietly, like he’s just realized that he has to sit through the rest of the meeting, and Dean snorts against his hair. 

“Having fun?” he asks. He takes that moment to rock his leg just a little, and he feels Sam’s hard cock press against his thigh. Sam’s thighs tighten up around him, locking his leg in place, but Dean’s already got his answer. 

“Slut,” he whispers affectionately, and Sam just shifts and wraps himself around Dean tighter. 

“Asshole,” Sam shoots back.

Dean doesn’t really hear the rest of the meeting, but that’s okay; Castiel can fill him in later. 

Right now though?

Dean just grins and pulls Sam close, pushes his leg up just a little, hiding Sam’s squeak against his shoulder. 

This is gonna be a fun meeting.

\---

“Holy fuck,” Sam gasps, slamming the door shut behind them. Dean turns on him, an amused smile on his face, but it quickly sharpens into something more heated, more intense. Sam’s flushed red and he’s squirming, looking up at Dean with his lips bitten raw and his eyes wide and wet. 

“God, _please_ let me come,” he begs. 

“Show me you deserve to,” Dean says, eyes darkening. “Wanna see how wet you are.”

Sam scrambles onto the bed, sheets already rumpled and messy, a dirty wink at how much Sam’s been teasing himself for the past few hours. 

Sam was the one to ask about it, all big doe eyes and pouty lips and pink cheeks. 

“Wanna edge myself all day,” he’d whispered. “Get myself all desperate for you and then let you fuck me dry afterwards.” Dean had kissed him stupid and demanded he follow through.

Dean watches him now, sees the way Sam glances over his shoulder and grins at him all dopey. He’s shaking but it’s the good kind, the kind that betrays the pleasure that’s drilled itself into his bones, flooding through his body in a never ending stream. He’s close, has been for a while, and Dean wants so badly to shove him over that edge, to fuck the orgasm right out of his trembling body. 

_Soon_. He shivers with anticipation. 

Sam lowers his chest to the bed, hooks a thumb into the waistband of his jeans and tugs them down, exposes the soft pink lace covering his ass. He kicks his jeans down and off, letting them crumple to the floor, and he lets out this deep guttural sigh of relief that has Dean’s cock stirring in his own jeans. 

“Fuck,” Sam breathes. Dean approaches him then, slowly glides a hand across his panties, palming his cheeks. He pulls them open, slips a thumb in between and knocks against hard silicone, and he suddenly _needs_ to see what it looks like. 

This part had been Dean’s little addition. He’d left this morning on a supply run, but he’d left a present and a note behind for Sam, detailing that he could back out if he wanted and that this was only optional. 

By the time he’d come back, the box was open and gift wrap was everywhere and Sam was barrelling into him, flushed and sweating a little, kissing him hard as soon as he’d walked through the door. 

Dean slowly tugs his panties down past his ass, groans low in his throat. 

Sam’s asshole is glistening with lube, and it’s stretched open around a pretty pink buttplug.

It’s nestled sweetly against his soft skin, and Dean thumbs around it, dazed. He pushes a thumb against the flat of it, driving it deeper into his brother’s willing body, and Sam mewls, thighs tensing, and Dean can see his cock now too, hanging heavy and thick between his legs. 

Sam’s always been a leaker. Dean loves it, loves watching his cheeks flush whenever he calls him a girl for it, but this. This is different. 

He brushes a finger down the shaft, murmuring as Sam whines and jolts away. His cock is _hot_ , burning to the touch, slick with both lube and precome. 

“Shit,” Sam breathes, and Dean can see him tense up around his plug. “ _Shit_.”

“Does it hurt?” Dean asks. Sam hisses, rolls his hips back. 

“Yes but it-- god, it feels fucking good.”

“Tell me what you’ve done today,” Dean says, spreads his cheeks again to nose along the cleft, licking a stripe from his perineum to the edge of the plug. Sam moans, shifts his legs to balance better on the bed. His cock swings untouched under him. 

“Woke up and put in your plug,” he mumbles, grunts when Dean pulls at it, tugging it out slow just to push it back in. “Love it so much, De, thank you.”

Dean smiles, presses a chaste kiss onto Sam’s asscheek. Sam snorts, amusement bleeding into a whimper as Dean fucks the plug back in all the way, twisting it at the end. 

“Keep going,” Dean says. 

“Jerked off in the shower,” Sam gasps. “Came close but I stopped right before. God, it felt so good.”

“Yeah?” Dean pulls the plug out, watches Sam’s hole cling to it, winking once it’s out. Dean leans forward and licks into the gape, presses his tongue against his hot walls and lets his spit drip down to his balls. Sam cries out, rocks his hips back into it, and Dean gives his ass a quick slap to jolt him out of it. 

“G-grinded against the pillow next.” Sam curses and taps frantically at Dean’s scalp, tensing up and closing his legs a little when Dean eases off and pulls back. He’s just at the right angle to see Sam’s cock throb and pulse out a few drops of precome, dripping down onto the sheets. Sam slumps like all his muscles have given out, but his arms hold steady and it only takes a few moments for Sam to readjust his position and spread his legs again. 

“Fuck,” Dean breathes. “That’s fucking hot.” Sam laughs, a little strained. 

“The pillow or the edging?”

“Both,” Dean says. “All of it, Jesus.”

Sam smirks, rolls his hips in invitation. Dean doesn’t need any further convincing. He holds Sam’s cheeks open and licks right back in. Sam gasps, but he obediently picks up where he left off. 

“I used that dildo you bought me years ago,” he says. Dean pauses to ask, “The big one?” and Sam nods, smiling hazily. 

“It still stretches me out so much,” he says lowly. “Hits all the best spots.” Dean groans, points his tongue and fucks into Sam’s ass in quick thrusts. His finger worms its way in, and he’s searching for that spot in Sam’s body, the one he knows gets him hot and bothered in an instant. 

“Spent all day imagining it was you fucking me, big brother,” Sam pants, whines when Dean hits that spot hard. “Oh god, De, want your cock in me _now_.”

“You held off for this long,” Dean murmurs, eases up and works on stretching him instead. “Want you to edge one more time for me, princess, then I’ll let you come on my cock.”

Sam whimpers, nods his head into the sheets, and then Dean slips his fingers out and steps back, watches Sam like a hawk eyeing its prey. 

Sam breathes shakily, curls an arm under himself and feeds two fingers into his ass, slides them in smooth like a knife sinking into butter. His cock brushes his wrist and he hisses, arches his back just a little more. 

“Fuck,” Sam breathes. He slowly starts fucking his fingers in and out, tugging at his swollen rim with every push. He’s breathing hard, little moans slipping past his lips, and he speeds up to a jackrabbit pace, skin slapping against skin. It’s dizzying when he suddenly tugs his fingers out and clenches down on air, thighs shaking as his cock leaks clear against his wrist. 

“So good, babygirl,” Dean says, gliding soft palms up Sam’s thighs to squeeze his cheeks again. “You’re so wet, holy shit.”

Sam whines and kicks his knees apart, looks back over his shoulder with his eyelids at half mast. 

“Please, I wanna come on big brother’s cock.”

Dean mutters curses, unbuttons his jeans and shoves them and his boxers off his legs. He gives himself a few pumps, just to ease the pressure, but Sam’s all open and slick just for him and he’s only human. 

“Such a good slut, huh, Sammy?” He growls a little, low in his throat, and slaps the head of his cock against Sam’s hole. “Look at you, legs spread for your big brother.”

“Yes,” he gasps, moaning loudly with the next slap. “All for you-- oh _god_.”

And then Dean lines it up and pushes in, watching his entire length disappear into Sam’s body. Sam’s arms buckle and his jaw goes slack, but he opens up for it easy, lets him right into his slick heat. 

“‘M gonna, _fuck_ , I’m so fucking close.” Dean grunts and grabs his hips, dragging him back on his cock and thrusting forward in one rough shove. Sam shouts, clenches tight, and Dean growls and digs his fingers in hard. 

“Hold it,” he demands. “Don’t you dare come until I say so.”

Sam’s trembling around him, silent if not for the stuttered gasps he’s letting out, but he drops his head between his shoulders and slumps. 

“Yes sir,” he says. 

Dean takes that moment to slam his hips forward again, spreading Sam’s cheeks to get deeper, to thrust harder, _faster_ , needing so badly to make Sam’s body shake in time with his. 

Sam’s obedient when he’s getting what he wants, and it fills Dean with some perverse satisfaction when Sam gasps and fists the sheets, fucking back against him, cock still leaking and untouched under him. 

“Think you can come without touching your clit?”

Sam’s eyes flutter shut, and he gives a jerky little nod. Dean hums, thumbs absently at his puffy rim, feels his cock slide in and out, and Sam just shudders and takes it. 

“You’re so fucking tight,” Dean mumbles. “Sure you used that dildo today?” 

“Y-yes.” Sam whimpers at a particularly well-aimed thrust. Dean sets his feet and aims for that spot again, quirks his lips up when Sam shouts. “Dean, I can’t--”

“S’okay, almost there, angel.” Dean draws it out just a little more, grinds his hips in dirty circles, traces his rim with a light touch. Sam gasps, breathy and soft, and Dean grins. 

The rhythmic slap of skin on skin is loud in Dean’s ears, punctuated by gasps torn from Sam’s lips, and he’s squeezing around him so tight, so perfect. 

“Made for it, huh?” Dean breathes, leans forward to rut into Sam all sharp and nasty. “Pretty pussy was made to take my cock.” Sam groans high and throws his head back. Dean wraps a hand up in his hair and pulls it taut, keeps his back arched in that pretty curve. 

“Say it,” Dean gasps, slows down into a smooth grind, curling against his brother’s back, pressing deep into his ass. “Whose pussy is this?”

Sam’s heaving, shaking in his hold, and Dean feels his ass clench hard. When Sam speaks, his words leave him in a whoosh of air, broken and aching. 

“Yours, it’s yours.”

“Say it again.”

“Fuck, Dean,” his voice wobbles a little, “My, my pussy is yours. It’s _yours_.”

Dean groans and slams deep, waits for the familiar spasm of Sam’s hole, the quaking of his limbs, the jerk of his purpling cock, holds him there until he’s tipping, tipping--

“Come.”

Gone. 

It’s fucking _violent_ the way Sam arches back and screams, and it sounds like it’s being ripped straight from his throat, like he’s losing his goddamned mind. His ass goes python-tight around his cock, and he shoots off for what seems like hours, spilling and spilling and it doesn’t seem to be stopping. 

Dean fucks him through it, reaching around to fist Sam’s cock fast when he sobs for it. He’s soaking with precome, hot and wet, and it’s just the right slide for Dean to wring him dry. He aims his cock to hit his prostate, milking him from the inside out, and then Dean finally tenses up and comes hard, shoots deep into Sam’s ass, panting heavily. 

It’s a long while before Sam finally slumps onto the bed, boneless and completely spent. 

Dean pulls out slow, watches his come drip out of Sam’s ass with a glint in his eye. Sam’s glistening with sweat and still shaking through the aftershocks. Dean’s gentle with him when he curls his arms around Sam’s middle and tugs him further up the bed, settling him on his chest and against his side. 

Sam leans into him, noses at his chest and smiles distantly. Dean’s lips pull into a half-smile, eyelids drooping, and he kisses Sam’s hair softly. 

“Hey Sammy,” Dean says, grinning. “Feel okay?” Sam huffs into his neck, kisses a vein. 

“‘M good,” he says quietly. “Thank you, De.” Dean scoffs and curls a hand in his hair, massaging little circles into his scalp where he’d pulled his hair. 

“Jesus, I should be thanking you.” Sam hums, nuzzles against his adam’s apple and sighs, and Dean just laughs, twining his legs up with Sam’s. 

“Love you, Sammy.”

“Love you too, De.” 

Dean grins, slides a hand down to rub his ass soothingly. “You gonna do this again?”

Sam laughs, wraps a hand around Dean’s waist, and Dean watches him blush and flutter his eyes shut. 

“Absolutely.”

Dean combs gently through Sam's hair with a fond little smile on his face. He likes those odds. 

\---

“You _what_?” 

Dean smiles sheepishly, lifts and drops a single shoulder. 

“I, uh, wasn’t paying attention?” Bobby pinches the bridge of his nose, grumbles something under his breath that Dean can’t pick up on, and then he just throws his hands up and leaves the room, shaking his head. Castiel’s fighting to hide his smile, but then Dean catches his eye and cracks a grin and they’re both cackling, loud and long and gut-deep. 

“Jesus, it’s been a while since Bobby’s been that pissed.” Dean chuckles. “Maybe I should formally apologize this time, write him a note and toss some cash in it as reparation.”

“I doubt he’d be against that,” Castiel muses with a sly smile, staring at the door. “Perhaps I should detail the plan for you again?” 

“Nah,” Dean says, rolling out the cricks in his neck. “You said Kevin’s on it, right?”

“Yes.”

“And Sam’s gonna nose his way in to help him?”

“Definitely.”

“Then I’m not worried.” Dean leans back in his seat. “We have two smartasses on it already; I don’t think I’m needed right now. Besides,” he smirks. “Sam can always fill me in later, once his stupidly big brain is satisfied with every single detail.” Castiel hums, tucks his hands away in his pockets. 

“I suppose that is fair.”

And then, like clockwork, Dean and Castiel watch Sam scamper past the door, eyes fixed firmly ahead of him, and Dean knows without a shadow of a doubt that the kid’s looking for Kevin. He glances at Castiel and finds the same understanding dawning in his eyes. 

“So,” Dean says, kicking up his feet and folding his arms behind his head, cocking his head and an eyebrow. “Wanna play poker?”

Castiel rolls his eyes, but Dean knows it’s a ploy because Castiel hasn’t declined a game of poker since the day Dean met him. 

And later, when Sammy creeps back into the room and wiggles his way onto Dean’s lap in the middle of the game, eyes bright with mischief, well. 

Dean just pulls him close and readjusts the straight flush in his hands. It’s a win-win, really. 

.


End file.
